The One with the Pimp and the Ho's
This has not aged well.
Harry Mudd is a con man who is bringing his cargo, 3 beautiful women, to potential buyers. Kirk wrecks his engines saving Mudd and is at his mercy when they reach the mining colony as the miner's want only one thing - women
This is really bad. Mudd is clearly meant to be a fun, roguish character who's a bit cheeky. he's not. He's a Man who traffic's women and has them addicted to a drug called Venus which keeps them young and "beautiful". He's an Arsehole basically.
Not only that, but kirk comes over looking weak and ineffective as he practically pleads with Mudd to let the Miners deliver the crystals or the Enterprise is doomed. Now, I know he can't go in all guns blazing and simply take them, but there comes's point when kirk would rip up the rule book and put a phaser to Mudds head to save his crew and ship. He's not exactly shy at bending the rules. But no, in this episode, he's running round like a headless chicken.
The final nail is when Kirk gives Eve the placebo that gives her magically a new hairdo, make up and shiny glow, when moments ago she looked ancient and sexy as a chimney sweep.
The only good moments are McCoy and Scotty's reactions to the women, but really awful episode.